ethyl 8-[(S)-[4-(benzyloxy)phenyl](hydroxy)methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylate

• ChemBase ID: 170279
• Molecular Formular: C25H30O6
• Molecular Mass: 426.5021
• Monoisotopic Mass: 426.20423868
• SMILES: [C@H](C1(CCC2(CC1)OCCO2)C(=O)OCC)(O)c1ccc(cc1)OCc1ccccc1
• Canonical SMILES: CCOC(=O)C1(CCC2(CC1)OCCO2)[C@H](c1ccc(cc1)OCc1ccccc1)O
• InChI: InChI=1S/C25H30O6/c1-2-28-23(27)24(12-14-25(15-13-24)30-16-17-31-25)22(26)20-8-10-21(11-9-20)29-18-19-6-4-3-5-7-19/h3-11,22,26H,2,12-18H2,1H3/t22-/m0/s1
• InChIKey: LHQREPLLEPMRRW-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 8-[(S)-[4-(benzyloxy)phenyl](hydroxy)methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylate
• IUPAC Traditional name: ethyl 8-[(S)-[4-(benzyloxy)phenyl](hydroxy)methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylate
• Synonyms: 8-[(S)-Hydroxy[4-(phenylmethoxy)phenyl]methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylic Acid Ethyl Ester; 8-[(S)-Hydroxy[4-benzyloxyphenyl]methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylic Acid Ethyl Ester

Database IDs

• CAS Number: 182227-19-6
• PubChem SID: 164226189
• PubChem CID: 10526461

CALCULATED PROPERTIES

• Acid pKa: 13.769907
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.100066
• LogD (pH = 7.4): 4.100066
• Log P: 4.100066
• Molar Refractivity: 115.8889 cm^3
• Polarizability: 45.84777 Å^3
• Polar Surface Area: 74.22 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate

DETAILS

Toronto Research Chemicals - H829950

Intermediate in the synthesis of a cholesterol absorption inhibitor.

REFERENCES

• Wu, G. & Tormos, W.; J. Org. Chem. 62, 6412 (1997)